The Southern Heart of New Hampshire

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5 Day(s)
180 Miles
avg 60 Miles

Tour operator:  Ciclismo Classico

Exploring the Historic Villages, Lovely Lakes and Bucolic Byways of Southern New Hampshire.

The National Trust for Historic Preservation has added Keene to its list of “America’s Dozen Distinctive Destinations,” calling it a “Currier & Ives landscape come to life.” Join Director Lauren Hefferon in her hometown and discover the rich history, pristine landscapes, and gorgeous backroads that inspired her passion for bicycle travel. In every direction, the roads and hamlets along the way connect and lead us to stories of an era and people that formed the foundation of a highly independent and hardy culture determined to rebel from England and establish themselves as among the most self-reliant in America, thus the state’s motto, Live Free or Die. New Hampshirites take their role of protecting their land seriously maintaining some of the most intense conservation programs in the country.  Keene is the heart of the picture-perfect Monadnock region, known as NH’s cultural corner that is a perfect cycling base offering a variety of gorgeous loops for all cycling abilities. Lauren has selected her favorite cycling loops from Keene that include a dive into the colonial and Native American past of North America. Each day you’ll experience mile after mile of gorgeous scenery and a glimpse into the connective tissue of our nation’s past. Pedal past and learn about the fascinating  historic architecture, art galleries, covered bridges, abundant lakes, cool forests, zigzagging rivers, farmland galore and daily views of the region’s crowned granite jewel, Mt Monadnock, (Mountain That Stands Alone) the second most climbed mountain in the world. Known for its presence in the writings of Ralph Waldo Emerson and Henry David Thoreau, it is the most prominent mountain peak between the White Mountains of New Hampshire and the Massachusetts Berkshires. We are based for four nights in downtown Keene,  a charming and eclectic mix of old-time shops, modern retailers, restaurants and cool coffee shops. Recently Keene has added 15 stunning historical “Walldog”murals to its downtown landscape that beautifully depict the region’s historic resources and rich cultural heritage.  Keene is framed by one of the most beautiful Main Streets in the world with the picturesque (and much photographed) United Church of Christ at the top of Keene’s Central Square.  For photography fans, Lauren will be stopping to show you all of the most photogenic hot spots and for the gravel hungry we have dedicated one day to recreate a mini Eroica experience. 


Tour Location

New England
Keene, New Hampshire
Keene, New Hampshire

Tour Information

Supported, Bring your own bike
5 Day(s)
Some hills
Double Occupancy
Cost From:
USD 1850
Single Supplement:

Tour Distance & Dates

180 Miles
Riding Days:
September, October

Additional Information


Double Occupancy / Twin Share

Single Supplement: $440


All accommodations (4 nights at Fairfield Inn and Suites)
All breakfasts, 1 lunch, 3 dinners
Van support
2 experienced guides


MILEAGE Average Daily: 29-6 0Total: 115-200
Any of our tours can be made private if you prefer to travel ONLY with your friends or family - contact us.

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